“What would the corporation’s CEO wake up in the middle of the night thinking about? What would disrupt his $1 billion business?” Hyde Park Angels Managing Director Peter Wilkins posed during a Sept. 24 collaborative program between HPA and 1871.

After answering that, noted the panelists onstage with him, the startup had better be able to prove their solution not only works, but would work at large scale – if only the entrepreneurs had the business model and production channels enjoyed by a potential enterprise partner.

The program, “Connecting Corporations and Startups,” was the third of four in HPA’s Entrepreneurial Education Series with 1871.

The first two sessions in March and June covered how entrepreneurs can tell if they’re ready to raise their first funding round, followed by an overview of early-stage investment. The final program, on Thursday, Nov. 12, will be on “How to Work with Advisers, Board Members and Investors.” (Get tickets here to future Hyde Park Angels programs.)

That the series and its subject matter are being hosted by HPA at all — particularly on corporate venture partnerships – points to more bedrock considerations on the fundamentals of early-stage investment in Chicago and the Midwest.

The Sept. 24 panelists were a good representation of startup-and-corporation match-making in Chicago. Julie Szudarek is SVP and General Manager of Groupon Daily Deals. Rumi Morales is the Executive Director of the Strategic Investment Group at CME Group. Jacob Babcock is the Co-Founder and CEO of wireless charging antenna startup NuCurrent, and his corporate connection Rob Diebold is the Strategic Business Development Manager at Molex.

Rounding out the panel were Illinois CIO Hardik Bhatt, who headed the Cisco Smart Cities and Internet of Things groups before going to work for the state (and thanks to a budget impasse, so far, for free), as well as David Weinstein, the Founder and Managing Partner of Freshwater Advisors who, with the Illinois Science and Technology Council, helped kick-start the process of pairing Illinois corporations with startups to drive connections and plug gaps in the armor of corporate technology and innovation.

That the series and its subject matter are being hosted by HPA at all — particularly on corporate venture partnerships – points to more bedrock considerations on the fundamentals of early-stage investment in Chicago and the Midwest.

Namely, the money that entrepreneurs expect from early sources and second venture rounds isn’t there in the Midwest without atypical venture funding – such as corporate venture funds or coastal partnerships.

Meanwhile, early investors in the Midwest and elsewhere don’t see enough deal flow to merit the historically high valuations they’re seeing for startups.

The fundamentals need a better look.

The series marks a turning point for Hyde Park Angels under Wilkins, who took the helm at the rapidly growing HPA as it morphs from a confederation of gun-slinging early-stage investors to what he’s now positioning as a community-oriented civic organization seeking to actively improve fundamentals within the Midwest’s entrepreneurial ecosystem. (Turning a buck is still in vogue, he says.)

The program’s setting may have been 1871, but the backdrop still included increasingly familiar cries from angel funders and early-stage investors – some of them in the audience. The market has pushed startup valuations unreasonably high.

In the latest CFO Magazine, the size of valuations facing corporate venture funds were compared to the dot-com boom. Many investors have started to use the word “bubble.”

Meanwhile, the fastest-growing and bravest money in the Midwestern marketplace right now may well come from corporate venture coffers – at least they’re willing to spend.

The caveat, according to the report, to CFO Magazine, to the lessons of the dot-com era – and to common sense – is that corporate ventures do better when they’re for strategic reasons than for pure-play investments.

In a room like 1871, there’s something fascinating about the mutual curiosity. Especially in the Midwest, which is traditionally heavy on B2B-startups and light on venture capital.

Periodically, Wilkins polled the audience. The hands-up statistics were compelling.

About 23% of the 150 people in attendance (by show of hands and the wearing of suits) were interested in corporate venturing or strategic partnerships. Current or aspiring entrepreneurs (who also were willing to raise their hands, and who wore more t-shirts) made up about 34% of the room. A third of the room was undeclared.

Audience members may have felt like an enterprise company looking for startup partners. Or an entrepreneur looking to scale up by partnering with corporate incumbents.

Either way, the undertone about fundamentals rang loudly enough for anyone who cared to listen.